Your Career Isn't a Straight Line
Career changes aren't about starting over—they're about rerouting with everything you've already learned.
We often describe career changes as “starting over,” but we rarely start from zero. Every role leaves us with skills, relationships, confidence, and lessons that travel with us. Sometimes we aren't starting over at all; we're simply rerouting.
Think back to that moment when you were entering the workforce for the first time. You probably had stars in your eyes, thinking about all the money you'd be making because, let's face it, if you started working at 16, that was the goal, right?
But let's look at your first “big girl” job. You may have entered the workforce with a set plan in place, ready to conquer the world. Then there are those who enter the workforce by necessity, and their careers find them rather than the other way around. What sets them apart? Sometimes, it's simply the route they took to get where they are.
Looking back at my own journey, I remember being a little girl and driving through downtown Houston, Texas. I would look up at those amazing skyscrapers and tell my mom, “I'm going to work in one of those buildings someday.” As I grew older, I kept that dream. I wasn't sure what I would do there; I just knew I wanted to be part of that fascinating world.
My personal life took a different path when I decided to get married right out of high school rather than pursue my dreams and go to college. Five short years later, I was a single mom, wondering what I would do with my life and how I would support my children.
Thanks to a workforce training program, I was offered the opportunity to take some college courses and earn an office certification that would allow me to enter the workforce as a secretary. I jumped at the opportunity. Not only did I excel, but I also achieved the dream I'd had as a little girl: I began working in one of those high-rise buildings in one of the biggest cities in the United States.
That first job as a secretary for a commercial real estate firm was not my forever dream, but it was a step toward figuring out what that dream really was. That journey of discovery would take me down several different paths over the years. You see, while I had achieved my dream of working in downtown Houston, that job opened an entirely new world of discovery for me and challenged me in ways I could never have imagined.
Within two years, I had moved from secretary to assistant commercial property manager. That wasn't part of the plan. Honestly, at that point in my life, I don't think I even knew enough about commercial real estate to know it could be part of the plan. Someone gave me an opportunity, I learned, I grew, and suddenly the road in front of me looked different.
That became a pattern throughout my career.
More than a decade later, life circumstances took me away from commercial real estate and eventually landed me in a position as an actuarial assistant. If you're wondering how someone goes from commercial property management to actuarial work, you're beginning to understand my point. Careers don't always make sense while we're living them.
But that position led to another opportunity. I was recruited by a startup to help build its training department, and something clicked. I discovered that I loved helping people learn. I loved taking something complicated, figuring it out, and then helping someone else understand it. Eventually, I moved into leadership and began managing a team.
I didn't know it at the time, but another piece of my future career had just fallen into place.
My path shifted again when I moved into higher education and spent several years working in financial aid leadership. Eventually, I stepped away from the workforce for a time so I could focus on finishing my degree. While I was working toward that goal, someone asked me a question that would change the direction of my career yet again.
“If you could have your dream career, what would it be?”
“Teaching,” I answered.
“Then why don't you do that?”
It was such a simple question, but it stopped me in my tracks. Why didn't I? I had spent years learning how to adapt, how to lead, and how to teach others in the workplace. Maybe the dream wasn't as far away as I thought.
So I took the challenge. I earned an alternative teaching certification and, in the fall of 2013, walked into my first high school English classroom. I had rerouted again, and this time I thought I had finally arrived at my forever career.
Then life changed the route for me.
Years later, when my doctor looked at me and said, “You may need to rethink your career choice,” I was devastated. This time, I wasn't changing careers because another opportunity had come along. I wasn't chasing a promotion or wondering what else might be out there. This reroute wasn't my choice.
Teaching was having a serious impact on my health, and as much as I didn't want to hear what my doctor was telling me, I had to listen. Leaving the classroom was heartbreaking because teaching wasn't simply another job I had tried. It was my passion.
So I did what I'd unknowingly been practicing my entire career.
I rerouted. Or, in my best Ross Gellar voice, I had to “PIVOT!”
I was already working toward another master's degree, so I shifted its focus toward business and began thinking about what came next. Instead of asking myself what job I could start over in, I began looking at everything I already knew. I knew how to manage. I knew how to teach. I understood operations. I knew how to learn new systems, solve problems, communicate, and help other people understand complicated information.
Eventually, that pivot led me to professional development and learning technology. And somewhere along the way, I realized something important: I hadn't actually left education behind.
My classroom had simply changed.
Today, I still get to help people learn. I work with learning technologies, professional development, digital courses, systems, processes, and emerging tools like artificial intelligence. I manage a learning platform that allows others to better their careers and pursue their dreams. I learn new technology and then turn around and help others understand how to use it. The setting is different from my high school English classroom, but the part of teaching I loved most—helping someone understand something they didn't understand before—is still very much a part of who I am.
Looking backward, I can see that none of those earlier stops in my career path were wasted time. Commercial real estate taught me operations, customer service, and problem-solving. Corporate training taught me how to develop people. Leadership taught me how to guide a team. Higher education strengthened my understanding of service and education. Teaching made me a better communicator and showed me how differently people learn.
Every version of my career gave the next version something she needed.
Maybe you're reading this because you're considering a career change. Maybe the change wasn't your idea at all. Maybe a layoff, a health issue, a family responsibility, a relocation, or simply the realization that you want something different has put a roadblock in front of the path you thought you were supposed to follow.
Don't look at everything behind you as wasted time.
Take inventory.
What did you learn? What are you good at now that you weren't five years ago? What relationships did you build? What problems did you learn to solve? What did you discover about yourself?
Pack those things. They're coming with you.
Your next chapter doesn't require you to erase the chapters that came before it.
I'm no longer the secretary looking out the window of a Houston skyscraper. I'm no longer the commercial property manager, the actuarial assistant, the training manager, the financial aid manager, or the high school English teacher.
And yet, in some ways, I'm still every one of them.
Each version of me taught the next one something she needed to know.
So, if you're standing at a crossroads wondering whether it's too late to start over, maybe you're asking yourself the wrong question.
You don't have to start over. You may simply need to reroute.
